Metoclopramide

Basic Info

Common NameMetoclopramide(F05949)
2D Structure
FRCD IDF05949
CAS Number364-62-5
PubChem CID4168
FormulaC14H22ClN3O2
IUPAC Name

4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide

InChI Key

TTWJBBZEZQICBI-UHFFFAOYSA-N

InChI

InChI=1S/C14H22ClN3O2/c1-4-18(5-2)7-6-17-14(19)10-8-11(15)12(16)9-13(10)20-3/h8-9H,4-7,16H2,1-3H3,(H,17,19)

Canonical SMILES

CCN(CC)CCNC(=O)C1=CC(=C(C=C1OC)N)Cl

Isomeric SMILES

CCN(CC)CCNC(=O)C1=CC(=C(C=C1OC)N)Cl

Synonyms
        
            Metaclopromide
        
            metoclopramide
        
            364-62-5
        
            Metochlopramide
        
            Methochlopramide
        
            Metaclopramide
        
            Primperan
        
            Reliveran
        
            Reglan
        
            Metoclol
Classifies
                

                  
                    Predicted: Illegal Additives
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassPhenol ethers
SubclassAminophenyl ethers
Intermediate Tree NodesNot available
Direct ParentAminophenyl ethers
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsAminophenyl ether - Methoxyaniline - Phenoxy compound - Anisole - Methoxybenzene - Aniline or substituted anilines - Alkyl aryl ether - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Tertiary aliphatic amine - Tertiary amine - Organic 1,3-dipolar compound - Carboximidic acid - Carboximidic acid derivative - Propargyl-type 1,3-dipolar organic compound - Ether - Organopnictogen compound - Organic oxygen compound - Amine - Organic nitrogen compound - Hydrocarbon derivative - Primary amine - Organohalogen compound - Organochloride - Organonitrogen compound - Organooxygen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as aminophenyl ethers. These are aromatic compounds that contain a phenol ether, which carries an amine group on the benzene ring.

Properties

Property NameProperty Value
Molecular Weight299.799
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count7
Complexity300
Monoisotopic Mass299.14
Exact Mass299.14
XLogP2.6
Formal Charge0
Heavy Atom Count20
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9713
Human Intestinal AbsorptionHIA+0.9790
Caco-2 PermeabilityCaco2+0.8866
P-glycoprotein SubstrateSubstrate0.7687
P-glycoprotein InhibitorNon-inhibitor0.8782
Non-inhibitor0.8783
Renal Organic Cation TransporterNon-inhibitor0.7276
Distribution
Subcellular localizationMitochondria0.8278
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8602
CYP450 2D6 SubstrateSubstrate0.8918
CYP450 3A4 SubstrateSubstrate0.6375
CYP450 1A2 InhibitorInhibitor0.9107
CYP450 2C9 InhibitorNon-inhibitor0.9071
CYP450 2D6 InhibitorInhibitor0.8931
CYP450 2C19 InhibitorNon-inhibitor0.9025
CYP450 3A4 InhibitorNon-inhibitor0.9099
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6223
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8367
Inhibitor0.8579
AMES ToxicityNon AMES toxic0.5378
CarcinogensNon-carcinogens0.6142
Fish ToxicityHigh FHMT0.8688
Tetrahymena Pyriformis ToxicityHigh TPT0.9389
Honey Bee ToxicityLow HBT0.8515
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.8050
Carcinogenicity (Three-class)Non-required0.5827
Model Value Unit
Absorption
Aqueous solubility-3.1175LogS
Caco-2 Permeability1.2230LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.6332LD50, mol/kg
Fish Toxicity1.2793pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.4264pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
HoneyJapan0.005ppm
Other Aquatic AnimalJapan0.005ppm
CrustaceansJapan0.005ppm
Shelled MolluscasJapan0.005ppm
Other FishJapan0.005ppm
PerciformesJapan0.005ppm
AnguilliformesJapan0.005ppm
SalmoniformesJapan0.005ppm
Other Poultry,EggsJapan0.005ppm
Chicken,EggsJapan0.005ppm
Other Poultry Animals,Edible OffalJapan0.005ppm
Chicken,Edible OffalJapan0.005ppm
Other Poultry Animals,KidneyJapan0.005ppm
Chicken,KidneyJapan0.005ppm
Other Poultry Animals,LiverJapan0.005ppm
Chicken,LiverJapan0.005ppm
Other Poultry Animals,FatJapan0.005ppm
Chicken,FatJapan0.005ppm
Other Poultry Animals,MuscleJapan0.005ppm
Chicken,MuscleJapan0.005ppm

References

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Interaction Between 2 Nutraceutical Treatments and Host Immune Status in thePediatric Critical Illness Stress-Induced Immune Suppression ComparativeEffectiveness Trial.JPEN J Parenter Enteral Nutr2017 Nov27660289
Using Chemoinformatics, Bioinformatics, and Bioassay to Predict and Explain theAntibacterial Activity of Nonantibiotic Food and Drug Administration Drugs.Assay Drug Dev Technol2017 Apr28346800
Hepatopathy following consumption of a commercially available blue-green algae dietary supplement in a dog.BMC Vet Res2015 Jun 1926087767
Single-step multiresidue determination of ten multiclass veterinary drugs inpork, milk, and eggs using liquid chromatography with tandem mass spectrometry.J Sep Sci2015 Aug26033853
Understanding variability in posaconazole exposure using an integrated populationpharmacokinetic analysis.Antimicrob Agents Chemother2014 Nov25199779
Acetylcholinesterase inhibitors as pretreatment before acute exposure toorganophosphates: assessment using methyl-paraoxon.CNS Neurol Disord Drug Targets2012 Dec23244429
Delayed gastric emptying: whom to test, how to test, and what to do.Curr Treat Options Gastroenterol2006 Jul16836948
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Evidence that the anorexia induced by lipopolysaccharide is mediated by the 5-HT2C receptor.Pharmacol Biochem Behav2003 Jan12479973
Metoclopramide and (or) cimetidine administration to sheep fed tall fescue.Vet Hum Toxicol1996 Jun8727213
Lack of effect of NaCl and/or metoclopramide on exogenous (13C)-glucose oxidationduring exercise.Int J Sports Med1996 Apr8739568
The effects of endophyte-infected tall fescue consumption and use of a dopamineantagonist on intake, digestibility, body temperature, and blood constituents in sheep.J Anim Sci1993 Jan8454539
Potentiation by low doses of selected neuroleptics of food-induced conditionedplace preference in rats.Psychopharmacology (Berl)19937870917
Pharmacokinetic interactions of cefprozil with food, propantheline,metoclopramide, and probenecid in healthy volunteers.J Clin Pharmacol1992 Aug1487562
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